Taking the “See What Happens” Approach to Traveling (and Life)

Example A.Picture this: You’re on a four day trip to Barcelona, by yourself. You’ve mapped out every sight you want to see, restaurant you want to visit, and person you want to meet. You’ve created a jam-packed day-by-day itinerary because success to you is seeing as much of the city as quickly as possible. By day two, you’re a bit cranky due to jet lag, long lines outside La Sagrada Família, and a general feeling of being rushed. You keep pushing yourself, ignoring your discomfort, so you can see and do everything on your list. By day four, you’re completely exhausted, carrying a completed check-list, and experiencing a feeling that something is missing. You’ve crossed off your to-do’s but don’t have any memorable stories to accompany your travels.

Example B.Picture this: You’re on a four day trip to Barcelona, with your best friend. Each of you has picked a few must-see places to visit, keeping in mind that the motto of your trip is to “see what happens.” This is an adventure, you have an idea of where you want to go, and you feel open to where the journey takes you. By day two, you’re feeling energized by your half-day at the beach, 360-degree hotel rooftop wine-tasting, and photo excursion in El Born district. You randomly stumble upon a delicious tapas bar and interesting group of locals who convince you to go dancing with them late into the night. It turns out your new friend owns a vineyard estate fourty-five minutes outside the city, and they invite you to their second home for an authentic Spanish meal and wine-tasting experience. After four days, you leave the city inspired and invigorated, with new friends, a dozen stories, and a feeling that you got so much more than you were expecting.

If you ask me, it’s pretty damn clear what option I’d take. That’s taking the “see what happens” approach — which I’m always 100% onboard with. Truth be told, I can confidently say I’ve never planned out my whole itinerary prior to arriving somewhere, and have no plans to do so anytime soon (or ever for that matter).

Drew Meyers is the co-founder of Horizon & Oh Hey World. He worked for Zillow from September of 2005 to January of 2010 on the marketing team managing Zillow’s API program and various online partnerships. Founder of Geek Estate Blog, a multi-author blog focused on real estate technology for real estate professionals, and myKRO.org, a blog devoted to exploring the world of microfinance. As passionate as you get about travel.